Top Realtors and Real Estate Agents in Winchester, KY
Rankings based on verified MLS transaction data. Last updated September 2026. No pay-to-play.
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Top Agent
Top 2%
in Winchester, KY
$42.9M
All-Time Sales
$140K - $650K
Price Range
6%
Negotiated Off List
Top AgentTop 2.8%
in Winchester, KY
$173.8M
All-Time Sales
$230K - $1.4M
Price Range
5%
Negotiated Off List
Top AgentTop 3.2%
in Winchester, KY
$447.6M
All-Time Sales
$190K - $2.2M
Price Range
7%
Negotiated Off List
Top Agent
(152)
Terra Long
Keller Williams Greater Lexington
9 Years of experience
53+ Sales in the last 12 months
Top 3.6%
in Winchester, KY
$186.8M
All-Time Sales
$190K - $1.1M
Price Range
3%
Negotiated Off List
Top AgentTop 5.2%
in Winchester, KY
$16.7M
All-Time Sales
$160K - $780K
Price Range
Top Agent$50.9M
All-Time Sales
$180K - $1.9M
Price Range
5%
Negotiated Off List
Top AgentTop 10.8%
in Winchester, KY
$373.1M
All-Time Sales
$190K - $1.2M
Price Range
6%
Negotiated Off List
Top AgentTop 11.6%
in Winchester, KY
$268.4M
All-Time Sales
$170K - $2.3M
Price Range
8%
Negotiated Off List
Top Agent(15)
Jon Bentley
Keller Williams Realty Greater Lexington
7 Years of experience
24+ Sales in the last 12 months
$32.5M
All-Time Sales
$220K - $580K
Price Range
4%
Negotiated Off List
Top AgentTop 12.8%
in Winchester, KY
$172M
All-Time Sales
$210K - $2.3M
Price Range
4%
Negotiated Off List
Top Agent(52)
Erin Hurst
Keller Williams Greater Lexington
15 Years of experience
27+ Sales in the last 12 months
$136.7M
All-Time Sales
$180K - $650K
Price Range
3%
Negotiated Off List
Top AgentTop 15.6%
in Winchester, KY
$151.1M
All-Time Sales
$170K - $1.9M
Price Range
13%
Negotiated Off List
Top Agent$139.7M
All-Time Sales
$160K - $2.5M
Price Range
10%
Negotiated Off List
Top Agent(51)
Daphne Jewell
Berkshire Hathaway Home Services
14 Years of experience
19+ Sales in the last 12 months
$108M
All-Time Sales
$170K - $650K
Price Range
5%
Negotiated Off List
Top Agent$224.6M
All-Time Sales
$120K - $780K
Price Range
5%
Negotiated Off List
Top Agent$116M
All-Time Sales
$170K - $1.1M
Price Range
2%
Negotiated Off List
Top Agent$39.1M
All-Time Sales
$170K - $1.1M
Price Range
9%
Negotiated Off List
Top Agent$26.7M
All-Time Sales
$90K - $940K
Price Range
5
Sold in Winchester, KY
Top Agent(18)
Rhonda Mohrmann
Keller Williams Greater Lexington
6 Years of experience
1+ Sales in the last 12 months
$10.4M
All-Time Sales
$170K - $540K
Price Range
5
Sold in Winchester, KY
Top Agent$113M
All-Time Sales
$160K - $600K
Price Range
6%
Negotiated Off List
Top Agent$103.8M
All-Time Sales
$170K - $1.3M
Price Range
6%
Negotiated Off List
Top Agent$160.3M
All-Time Sales
$150K - $1.3M
Price Range
7%
Negotiated Off List
Top Agent$22.6M
All-Time Sales
$140K - $700K
Price Range
3
Sold in Winchester, KY
Top AgentTop 19.6%
in Winchester, KY
$57.1M
All-Time Sales
$230K - $700K
Price Range
1%
Negotiated Off List
Top Agent$676.1M
All-Time Sales
$190K - $2.1M
Price Range
5%
Negotiated Off List
Winchester Housing Market Trends
Homes in Winchester take a median 52 days to sell, go for 97.65% of asking, prices are down 4.7% from a year ago. Verified MLS market data through September 2026.
Market temperature
Seller's market
2.6 months of supply. Under 3 favors sellers, over 6 favors buyers.
What homes sell for
$247,332
median sale price
How fast they sell
52 days
median time on market
Supply and competition
2.6 months
of supply on the market
The numbers speak
for Winchester.
Every agent above earned their place with closed sales, not advertising. Tell us about your home and our algorithm picks the Winchester agents whose results fit it.
Winchester agents analyzed for these rankings
days faster: top-ranked agents sell in 25 days, the Winchester market in 52
median sale price in Winchester
Do Top Winchester Agents Sell Faster?
The 25 top-ranked agents on EffectiveAgents in Winchester sell in a median of 25 days, compared with the Winchester market median of 52 days on market.
About 27 days faster (52% quicker than the Winchester market)
Median days to sale reported by the top-ranked Winchester agents on EffectiveAgents, compared with the Winchester market median days on market. Agent figures reflect each agent's reported sales history.
When Is the Best Time to Sell a House in Winchester?
Based on the last 24 months of verified MLS market data, homes in Winchester sell fastest and closest to asking when they go under contract in June. To hit that window, plan to list around May.
Median days on market by month (shorter is faster)
June
Best month to sell
44 days
Typical time on market
99.1%
Of asking price
Seasonal averages from the last 24 months of Winchester, KY sales. Individual results vary with price, condition, and how the broader market moves. A local agent can pinpoint the right timing for your home.
What These Numbers Mean for Winchester Buyers and Sellers
The Housing Market Trends module above establishes Winchester as a market measured at Seller's Market, and the competitive indicators point to a market where negotiating leverage is more balanced than it has been in recent cycles. With 2.6 months of supply and 64 active listings against 25 homes sold monthly, inventory sits in the range that typically keeps pricing power split between both sides of a transaction. The median sale price of $247,332 moved -4.7% year over year, and the median price per square foot measures $154.05.
The clearest signal for buyers is the share of listings with price drops, measured at 48.5%, combined with a median of 52 days on market. When nearly half of listings adjust their asking price and homes take that long to clear, buyers deciding how to offer have room to come in below list and request contingencies, particularly on listings that have aged past the two-week mark. Only 9.5% of homes sold above asking, and 21.7% went off the market within two weeks, so bidding wars are the exception rather than the rule.
For sellers, the implication is to price precisely at the outset. The average sale-to-list ratio of 97.65% shows sellers are collecting close to asking when they price correctly, but the high price-drop share indicates that overpricing leads to time on market and eventual reductions. With 250 licensed agents working the 40391 and 40392 zip codes, choosing one who reads these indicators accurately is what separates a clean sale from a prolonged one.
What Winchester Home Prices Mean for You
Understanding the true cost of homeownership in Winchester goes beyond the listing price. These calculators break down what today's market conditions mean for your budget, your timeline, and your negotiating position.
| Median home price | $247,332 |
| Down payment (20%) | $49,466 |
| Loan amount | $197,866 |
| Monthly payment (PITI) | $1,882 |
Based on 28% debt-to-income ratio, 7.40% mortgage rate (as of October 15, 2026), 30-year fixed loan, 1.15% property tax rate, $275/mo insurance. Actual requirements vary by lender.
Based on $247,332 median home price with 20% down at 7.40% (as of October 15, 2026) for 30 years. Property tax estimated at 1.15% of home value.
Year-over-year data reflects the most recent rolling period from Winchester MLS records. Prior year values calculated from current figures and published YoY changes.
What to Look for in a Winchester Realtor
Name recognition and advertising budgets tell you little about how an agent performs on price and timeline. The data worth weighing is closing volume, review depth, and the ability to negotiate within current conditions. Of the 250 licensed agents across Winchester, EffectiveAgents has ranked 58 based on measured transaction history. At the top of that analysis is Wayne Elkins at Remax Creative Realty, with 238 career transactions, 63 client reviews, and $42.9M in all-time sales volume. That track record matters in a market where 48.5% of listings cut their price and the average home sells at 97.65% of list. An agent who negotiates effectively protects that gap, whether representing a seller holding firm on a well-priced home in the 40391 zip code or a buyer pressing for concessions on an aged listing in 40392. When reviewing agents, read for patterns across multiple reviews rather than isolated praise, consistent mentions of pricing accuracy and communication are the most reliable indicators of repeatable results.
How We Rank Winchester Real Estate Agents
Our rankings are built from verified MLS transaction data, not advertising spend. For every agent we analyze more than fifteen performance signals, including sales volume in your city and zip code, recent and all-time transactions, days on market, negotiation results (how far above or below list price an agent's clients actually close), price-point fit, and verified reviews. The agents shown first are those whose verified results put them at the top of the Winchester market today.
Agents cannot pay for placement in these rankings. The underlying data refreshes as new closed transactions are reported, so rankings shift with real market performance. Learn how we rank agents.
250
agents analyzed
15+
performance signals
$0
paid for placement
Rankings reviewed by Kevin Stuteville, Licensed Florida Real Estate Broker (License BK3068131), Founder of EffectiveAgents.
Data last updated: September 2026
Winchester Real Estate Agent FAQs
Who is the best real estate agent in Winchester, KY?
The top-ranked agent in Winchester, KY based on EffectiveAgents analysis is Wayne Elkins at Remax Creative Realty, with 238 completed transactions, 63 client reviews, and $42.9M in all-time sales volume. EffectiveAgents ranks agents using verified transaction history, closing performance, and client review patterns rather than advertising spend, narrowing the 250 licensed agents in the area down to 58 ranked professionals. The best fit depends on your property type and goals, so comparing several ranked agents against your specific needs is the recommended approach.
How were these Winchester real estate agents ranked?
Rankings are built from verified MLS transaction data. We analyze more than fifteen performance signals for every agent, including sales volume in your city and zip code, recent and all-time transactions, days on market, negotiation results, price-point fit, and verified reviews. Agents cannot pay for placement.
How many real estate agents are in Winchester?
Our data covers 250 real estate agents serving the Winchester area. The count represents agents with transaction activity recorded in our Winchester market data, not simply everyone holding a license.
What does the median sale price in Winchester mean for sellers?
Winchester's median sale price is $247,332 as of September 2026. Half of recent sales closed above that figure and half below. It is a useful baseline for understanding the market, but an experienced local agent will price your home against comparable recent sales in your neighborhood, not the citywide median.
How long does it take to sell a house in Winchester?
Homes in Winchester take a median of 52 days to sell, and that figure reflects a +10 days change in market time compared with last year. Several factors influence where a given home lands relative to that median: pricing accuracy at listing, condition and updates, location within the 40391 or 40392 zip codes, and current inventory levels of 2.6 months of supply. With 48.5% of listings adjusting their price, homes priced correctly from day one consistently clear faster than those that require reductions.
Does it cost anything to use EffectiveAgents?
No. EffectiveAgents is free for home buyers and sellers, with no obligation to work with any agent we match you with.
Do agents pay to be ranked or featured?
No. Agents cannot pay for placement anywhere in these rankings. Positions are earned from verified transaction performance only.
What commission do Winchester realtors charge?
Commissions are negotiable and vary by agent, service level, and transaction. There is no set rate, and recent industry changes have made commission structures more flexible than ever. Discuss the structure directly with your agent before signing a listing or buyer agreement.
Should I use a local Winchester agent or a national brand?
The individual agent matters more than the brand on the sign. Offices within the same national franchise vary widely in performance, and the agent you hire, not the logo, prices your home, negotiates your contract, and manages your closing. A strong local agent brings firsthand knowledge of Winchester neighborhoods, pricing patterns, and buyer activity. Compare agents on verified local results such as recent sales, days on market, and negotiation outcomes rather than name recognition.
What questions should I ask a Winchester realtor before hiring them?
Ask how many homes they have closed in Winchester in the past year, what their average sale-to-list ratio is, and how much of their business is in your neighborhood and price range. Ask how they will market your home or find you listings, and how often they will communicate. Strong agents answer with specifics. Verified transaction data is the fastest way to confirm what you hear.
Top Realtors by Zip Code in Winchester, KY
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